(S,S)-2-(4-氯苯基)-3-硝基-1-苯基丙基膦酸二乙酯 | 1004794-69-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: (S,S)-2-(4-氯苯基)-3-硝基-1-苯基丙基膦酸二乙酯
• 英文名称: diethyl (S,S)-2-(4-chlorophenyl)-3-nitro-1-phenylpropylphosphonate
• 英文别名: 1-chloro-4-[(1S,2S)-1-[diethoxy(oxido)phosphaniumyl]-3-nitro-1-phenylpropan-2-yl]benzene
• CAS: 1004794-69-7
• 化学式: C₁₉H₂₃ClNO₅P
• 分子量: 411.822
• InChiKey: ZABSSBRQTSQGRY-RTBURBONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  87.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-nitro-2-(4-chlorophenyl)ethylene 、 苯基膦酸二乙酯 在 辛可宁 、 辛可尼丁 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 18.0h， 生成 (S,S)-2-(4-氯苯基)-3-硝基-1-苯基丙基膦酸二乙酯
  参考文献：
  名称：

  Effect of achiral and mixed chiral ligands on the asymmetric synthesis of γ-nitrophosphonates via Michael addition

  摘要：

  Changes in the diastereo- and/or enantioselectivity were observed when the Li-cinchonine catalyzed conjugate addition of phosphonates to nitroalkenes was carried out in the presence of achiral/chiral additives. Although the conjugate addition in the absence of such additives proceeded in better yields and selectivities as reported previously, the dramatic change in selectivity in the presence of additives provides an opportunity to synthesize different stereoisomers of the product, gamma-nitrophosphonate, using primarily the same chiral source. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.03.006

文献信息

• Cinchonine catalyzed diastereo- and enantioselective Michael addition of α-lithiated phosphonates to nitroalkenes
  作者：Vishal Rai、Shaikh M. Mobin、Irishi N.N. Namboothiri

  DOI：10.1016/j.tetasy.2007.11.001

  日期：2007.11

  Conjugate addition of α-lithiated benzyl- and alkylphosphonates to a variety of aromatic and heteroaromatic nitroalkenes in the presence of 50 mol % of cinchonine–Li catalyst system proceeded in high yields, diastereo- and enantioselectivities in most cases.

  在50 mol％的辛可宁-锂催化剂体系存在下，将α-锂化的苄基和烷基膦酸酯共轭添加到各种芳族和杂芳族硝基烯烃中，在大多数情况下，收率高，非对映和对映选择性高。
• Effect of achiral and mixed chiral ligands on the asymmetric synthesis of γ-nitrophosphonates via Michael addition
  作者：Vishal Rai、Irishi N.N. Namboothiri

  DOI：10.1016/j.tetasy.2008.03.006

  日期：2008.4

  Changes in the diastereo- and/or enantioselectivity were observed when the Li-cinchonine catalyzed conjugate addition of phosphonates to nitroalkenes was carried out in the presence of achiral/chiral additives. Although the conjugate addition in the absence of such additives proceeded in better yields and selectivities as reported previously, the dramatic change in selectivity in the presence of additives provides an opportunity to synthesize different stereoisomers of the product, gamma-nitrophosphonate, using primarily the same chiral source. (C) 2008 Elsevier Ltd. All rights reserved.